Sodium Carbonate → Methyl-2-formyl-7-methoxybenzo[b]furan-4-carboxylate

HRID 548971Notes

Reaction equation

HRID 548971 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([CH2:14]Br)[O:10][C:9]=2[C:8]([O:16][CH3:17])=[CH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-:19].[Na+].[Na+]>CS(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([CH:14]=[O:19])[O:10][C:9]=2[C:8]([O:16][CH3:17])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 66592982Methyl-2-bromomethyl-7-methoxybenzo[b]furan-4-carboxylate

Product 1

HCID 86636828Methyl-2-formyl-7-methoxybenzo[b]furan-4-carboxylateYield 90.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a well stirred solution of Methyl-2-bromomethyl-7-methoxybenzo[b]furan-4-carboxylate (step 6) (3.1 g, 10.36 mmol) in dimethyl sulfoxide (30.0 mL) was added powdered sodium carbonate (1.64 g, 15.55 mmol) at 90-95° C. and stirred for 2-3 hours. Reaction mixture was cooled to room temperature and diluted with water (300 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with water (2×50 mL) and dried over anhydrous sodium sulfate. Removal of solvent gave crude product (2.9 g) as brown viscous oil. Purification by silica gel column using chloroform: ethyl acetate (95:5) as an eluent afforded 2.2 g of pure product.

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic layers were washed with water (2×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of solvent
  6. customgave crude product (2.9 g) as brown viscous oil
  7. customPurification by silica gel column

Sources & evidence

ORD record
ord-8e834821abed4fe5ad094ba58cf0fed4
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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